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Jake Arrieta has emerged this year as something of a revelation, if not an outright ace, for the Chicago Cubs. Picked up last year in a flip deal involving Scott Feldman, Arrieta was long dreamed on by Baltimore Orioles fans and executives as a number one starter, but never really got there in that organization. The reasons are probably layered and nuanced – though I just like to think it was Chris Bosio magic and Arrieta’s own effort with the Cubs – but, for our purposes, what matters is that Arrieta always had the stuff, the makeup, and the build of a potential ace.

In other words, there are reasons to believe that this year’s performance – which is supported by great peripherals – is legit.

That’s good to hear, and certainly opens up the possibility of an extension with Arrieta, who is a Scott Boras client, and who heads into arbitration for the first time next year.

Figuring out a “fair” extension, however, is a little tricky. Arrieta, who turns 29 in March, doesn’t have a particularly long track record of this level of performance. But, man, this level of performance is truly impressive. With three arbitration years upcoming, the Cubs already control Arrieta’s age 29, 30, and 31 seasons on what amounts to the best kind of deal possible: three team options at an under-market price.

The question for the Cubs: do you want Arrieta’s age 32/33 seasons so badly that you’re willing to guarantee the payments for 29 to 31, AND guarantee something close to market price for ages 32 and 33? The answer there is almost certainly no, which is why there has to be a compromise on “market” value in order to get a deal together that makes sense. These situations can be tough, given the aging curve, and the fact that the Cubs already have Arrieta under control for his best and cheapest years.

From the Cubs’ perspective, the ideal extension is probably a three-year guarantee with a couple team options tacked on to the end. In such a deal, Arrieta guarantees that he’ll make good money over the next three years (if he is hurt or his performance slips, the Cubs can’t just non-tender him and save that money), and the Cubs pick up those options – which couldn’t be dirt cheap, but would have to offer some value – on the back-end.

But is that something Arrieta would consider? Would he really want to give up his possible crack at free agency for a short-term guarantee?

In his first pass at arbitration next year, Arrieta might make something like $4 million in 2015. Travis Wood, coming off his great year, got $3.9 million in his first arbitration go; Jeff Samardzija, coming off his first year as a starter in 2012, received just $2.64 million in 2013, his first arbitration year. To be sure, Arrieta’s performance this year has outdone both Wood and Samardzija, but neither of the latter two dealt with a shoulder issue in the season they broke out, and each logged more innings than Arrieta will likely be able to record this year. So, Arrieta gets a little more, but not much more.

From there, if Arrieta keeps up his ace-level performance, his 2016 arb salary could be in the $8 to $9 million range, and 2017 could top $13 million.

And from there, if we had to project his free agent value in 2018 (at age 32), it might approach $20 million. Again, that’s if he keeps up this level of performance, which is far from a given at this point.

Does a four-year, $35 million extension (with a club option for 2019 at $14 million) make sense for both sides? It’s not a huge investment for the Cubs, but it’s a rather healthy guarantee, given that there is some downside risk. The Cubs get a slight discount on each projected arb year, with the free agent year coming in at about $14/$15 million. I’m just spit-balling to get the conversation going.

All in all, an extension here is not something you rule out, but the final deal would have to reflect the reality of the Cubs control and Arrieta’s age/track record … but also Arrieta’s potential awesomeness. Given those inputs, can the two sides figure out a deal that makes sense? It’ll be tough, but not impossible.

Now we’ll see if it’s something the Cubs want to pursue. Maybe this is an offseason conversation while the sides are discussing Arrieta’s first arbitration salary anyway.

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